Phosphorus oxychloride → HCID 17832839, compound

HRID 1297589Notes

Reaction equation

HRID 1297589 reaction equation
[C:1]([CH2:4][C:5]1[CH:28]=[CH:27][C:8]([CH2:9][NH:10][C:11](=[O:26])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:7]([F:29])[CH:6]=1)(=O)[NH2:2].P(Cl)(Cl)(Cl)=O>>[C:1]([CH2:4][C:5]1[CH:28]=[CH:27][C:8]([CH2:9][NH:10][C:11](=[O:26])[C:12]2[CH:17]=[CH:16][CH:15]=[N:14][C:13]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:7]([F:29])[CH:6]=1)#[N:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10157629HCID 10157629, compound

Product 1

HCID 17832839HCID 17832839, compoundYield 39.7%

Conditions

Temperature
90 °C

Procedure

N-(4-Carbamoylmethyl-2-fluoro-benzyl)-2-(4-fluoro-phenoxy)-nicotinamide (0.290 g) was combined with phosphorous oxychloride (0.4 mL) neat, under nitrogen. The reaction mixture was heated to 90° C. for 2 h and then allowed to cool to ambient temperature. The reaction mixture was quenched with saturated aq. sodium carbonate (20 mL) and extracted with ethyl acetate (5×40 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography (ethyl acetate:hexanes=1:1) to yield the pure title compound (0.110 g).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe reaction mixture was quenched with saturated aq. sodium carbonate (20 mL)
  3. extractionextracted with ethyl acetate (5×40 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude product was purified by silica gel chromatography (ethyl acetate:hexanes=1:1)

Sources & evidence

ORD record
ord-7e1cccb1301a4a6c80f197c0641d13b2
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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